Although he can certainly drop a quick punchline, Chicago expat Kyle Kinane is, at this point in his career, a storyteller comedian. His 2010 debut comedy album, Death Of The Party (an A.V. Club favorite) is filled with lengthy tales that embellish simple comedy premises—like a boring day job, or getting pulled over by cops—with razor-sharp details and epic buildups that result in hilarious payoffs. The style seems to be working, too. Kinane, who now lives in Los Angeles and is one of Patton Oswalt’s tour-support favorites, was named one of Variety’s 10 comics to watch. He recently performed on Conan for the first time, and he now has a television pilot under his belt. The A.V. Club called him in mid-May to reflect on the evolution of his comedic style and stand-up career, and what lies ahead.

The A.V. Club:You started doing comedy while you were at Columbia College in Chicago, right?

Kyle Kinane: Yeah, I’d done one show at Zanies downtown. I read somewhere in a newspaper they were having an open casting call for comedy, so I did that. It was later at Columbia, about a year later or so, that I saw somebody in my classes that I saw at the comedy show. I was like, “Oh, hey.” I had no idea how comedy worked, I didn’t know where you started or that you could just do it, and so I saw that guy, who I still talk to. He said, “Oh yeah, there’s open mics everywhere.” He told me about all these places to go, and I started doing that, and that was ’99.

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AVC: Do you feel like there’s more widespread respect for comedy now than when you started?

KK: I would say yes, a lot more respect. There’s people like Mitch Hedberg. Just seeing him go, and it’s like, he’s not wearing a blazer and forcing a joke down somebody’s throat, he’s just doing his own thing. He was kind of independent of what I knew as comedy, and he’s one of the guys that made me think “Maybe I could do this too, if he somehow does it.”

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AVC: Early on, how did it go? Did things progress quickly? Did you bomb a lot?

KK: I’d say a pretty steady average of both. There were enough shows that gave me just enough hope to go keep doing this. “Let’s see what happens next week, you got enough laughs, let’s see what happens.” And then the next show would be a total embarrassment, and make me wonder why I even thought I could get on the stage and entertain somebody. And then the next show would be good, and then the next one would be bad. So it was this constant battle, and that’s why it’s still interesting. There’s still no guarantee that a show will go well, so that’s why it’s still the best thing in the world.

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AVC: Surely more of them are going well now, though, right?

KK: Yeah, the percentage is a little bit higher, but writing something new, especially if it’s not a formulaic—I mean, I don’t really have much of a formula to the writing, so it’s like, “Oh, this is something stupid I did again. I hope nobody’s sick of hearing me doing dumb shit, ’cause that’s all I got.” And that’s still what makes me excited to go perform. And like now, I’ll do nine shows at a club at 45 minutes, and by the end, I’m just sick of my own voice. I gotta go get into some kind of trouble so I have something to talk about next week.

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AVC: Were you always a storyteller, or did that come with time?

KK: No, it’s definitely one of those things I think develops. You gotta know how to write jokes, first and foremost. Some people are just fantastic bullshitters from day one. Everybody knows those guys—the ones in high school that you just wanna sit at a party and listen to tell a story. What happened, I was more proficient in the smartass department, so that’s how the comedy started. That, and the weird observations, the more Hedberg-esque, oddball one-liner observations. Especially when you start doing comedy, you’re only getting five-minute sets. So, okay, I got jokes. I gotta write jokes for five minutes. You’re focused on the shorter sets of your jokes. By default, they’re shorter, you want to get them in there, you want to get in as many laughs as you can in five minutes. When you’re starting, that’s what you translate into success, is how many laughs you get, as opposed to “Well, everybody listened to me for five minutes.” With longer sets, I guess I gotta stretch out some more. There’s a little bit more room to venture into stranger territories, and what starts developing is stories. It’s been fun. I still love a well-crafted joke. Twitter’s been great for that.

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AVC: Is this a style you think you’ll stick to, or do you see yourself moving away from that?

KK: Now that I headline, it allows me to do these things for 45 minutes. I just want to be cautious. Sometimes you see performers, and I think they rely a little too heavily on their reputation. You’ll see them just telling some story, and it’s like, “Despite who’s saying this, it’s just a shit story. It’s just boring, it’s not funny.” And people, I think, can get jaded thinking just because of who they are, somebody wants to hear it. And I hope I don’t get caught in that. I’m hardly a known name, but I don’t want to go, like, “Oh, people call me a storyteller comedian, let me just go up and just talk about my day.” I don’t want that to happen. But I do have fun doing it. I’ve got poison oak all over me, so I can tell them that tale.

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AVC: Judging by your Twitter comments, it seemed like we’d be hearing something about that from you eventually.

KK: Yeah, it took two weeks of me sitting with poison oak going, “I had better get something out of this goddamned thing.” The world has a way of allowing certain things to happen. You’re shopping for pajama bottoms, and you go, “Oh, this is it. This is where the story is. It’s this. Thank you, universe.” I mean, in a weird, backward way, I just embarrassed myself in front of strangers, but I know I can use this, whereas somebody else will just go home and be very sad. I’m like, “Yes! Awesome!” I welcome these moments. Sheer embarrassment, thank God.

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AVC: You moved to L.A. in 2003. When did you feel things started to take off?

KK: In 2007, I had on-paper success. I got to go to that Aspen comedy festival, which was pretty exclusive, I guess. Then I did Carson Daly. That was enough validation. I kind of had an unwritten thing; I was going to give myself until I was 30, and if I had no positive reinforcement to keep doing comedy, then that was the time to start looking for something else. And I turned 30 at the end of 2006, and then in February, I got word that I was gonna go to Aspen. And I was like, “All right, goddammit, time to invest myself.” But comedy’s always been just enough of an interesting, elusive ghost that even if it wasn’t a paying thing, I’d always be drawn to it some way or another.

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AVC: How did you end up hooking up with Patton Oswalt?

KK: That was probably around ’07 that I got to do one of the last shows at the old Largo here in Los Angeles, which is kind of this renowned comedy venue. And he was on the show, and he saw me there. It was also at the time I had gotten management, and these little things started happening, and it was the same manager, and then word came through them, like, “Yeah, they want you to open for him on some dates.” He had such an amazing fan base that there was really no nerves to even walk out cold in front of a theater; they were still very welcoming. He’s pretty unabashed when he picks an opener, like pimping them out to his fans. The audience knows that this person’s been approved by somebody they like. Some arms are crossed, like, “All right, you gotta prove yourself.” Some people are like, “Well, no, because you’ve made it this far, you’ve obviously jumped over the hurdles to get here.” They’re there to see a comedian. There’s other people I’ve opened for, instances where a lot of people are there to see somebody they know from a TV show, and they’re not really concerned about comedy, they’re just there to see a famous person. And so when the opener goes on, “Well, that’s not a famous person, what if we don’t give a shit about them?” But with his fans, they are comedy fans, so they’re there to see a comedy show that happens to be headlined by Patton Oswalt. They are open to seeing a comedy show, not just there to see a famous person do lines from a movie or from a TV show. So that’s the big difference with his crowd. I owe him a ton. That got me a lot of recognition, and it opened a lot of doors.

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AVC: How did February’s Comedy Central Presents special come about?

KK: It was a combination of a lot of things, especially last year. The album came out, I had just got the Variety “10 comics to watch.” Things just really came together last year, so I don’t know if it was because of that, or just involved with that. And also having management that’s involved and hands-on with things like that is nice. I’ve had previous experiences with just completely absentee representation. Things just all came together really well last year. And I’m scared shitless to find out how to keep momentum.

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AVC: How close are you getting to a new album?

KK: What I would like to have and what will happen are obviously two different things, but I would like by the end of the year to have a new album at least ready to record. I had 10 years of material to pick and choose from for the last one, because nobody knew who I was. Now I’ve got—on top of that, which was recorded in ’09, came out beginning of last year, I did a half-hour special that had different material on it than the album. Then I did the John Oliver special this year, which had a collection of about 15 minutes in addition to the mash-up special. So basically, all that material was another album in itself. That was another 45 minutes to an hour that came out after the album. I don’t want to repeat any of that, so it’s back to working on even more material. I don’t want to put it out there just to have it out there, I want it to be good. So once I feel it’s good, that’s when it will come out.

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AVC: You just wrapped a pilot, right?

KK: It was Matt Braunger’s pilot that he shot for Comedy Central. We were friends from back in Chicago. I play his sidekick in it. I managed to pull getting the role of “Kyle.” He just submitted it last week, I haven’t heard anything back yet about it. It’s one of those things, I hope for my best friend’s sake they pick it up. For my own well-being, I put that stuff out of my mind. It’s something that’s been shot and done, it’s not up to me. You see too many people like, “This thing’s gotta work out, if this doesn’t work out, I’ll just go nuts!” I don’t ever want to be like that. When he hears something, he’ll let me know. Right now, I’m just like, “We shot it, I hope I did a good job, I hope I didn’t embarrass myself or Matt for having me on his show.”

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AVC: Where do you want to take your career?

KK: I will welcome any kind of decent opportunity that comes my way. There are some voiceover things that have come up that I never particularly shot for, but the opportunity came up, and I’m like, “Yeah I’ll give it a shot.” Just like the thing with the pilot with Braunger, to act in that. I was like, “I don’t fancy myself an actor, but why not? Why would I not?” You know, as long as I feel like I’m not doing something that compromises any kind of beliefs or—I mean, I don’t have any kind of reputation, but as long as I can go to bed at night and I’m not doing a prank show, or tricking somebody and being mean, then why not try these things?